


Night Moves

by SupernaturalWinchester67



Series: Night Moves [1]
Category: Supernatural
Genre: Alternate Universe, Best Man Dean Winchester, F/M, Fluff and Angst, Friendship, Impala Sex, Smut, Wedding Night, Weddings, maid of honor reader
Language: English
Status: Completed
Published: 2018-12-06
Updated: 2018-12-06
Packaged: 2019-09-13 06:01:29
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 10,332
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16886973
Author URL: https://archiveofourown.org/users/SupernaturalWinchester67/pseuds/SupernaturalWinchester67
Summary: The reader hooks up with a guy she meets at a bar one night after she gets to the town where her childhood friend, Jess, is getting married in a few days time, leading to some unintended consequences…





	1. Chapter 1

In retrospect, you probably shouldn’t have chugged that first beer. It left you with your nose burning and a bubbling in your stomach where a burp was surely forming. You waved the bartender for another, gulping half that one down in one long swig. He raised a fast eyebrow and you ordered a shot of whatever the nearest bourbon was. By the time he’d poured, you were pushing over another empty bottle, the man putting a third in front of you without needing to be told.

You were thirsty. Water would’ve been a better option but after three delayed flights you needed a few. You were supposed to get in at noon, spend some one on one time with your friend before the wedding prep got her too busy to catch up. You sighed as you took your shot, the slight burn doing nothing to soothe your annoyance. It was after midnight and you were pretty sure she was in bed, rolling around with her fiancé, whispering silly things to one another.

The thought alone made you finish off your drink, forcing a long and low burp to escape. You thought you’d kept it quiet but the man at the other end of the bar was laughing to himself.

“Long day sweetheart?” he asked, leaning against the bar, throwing you a smirk. His eyes were a little hazy and you started to feel the alcohol hit you, making you braver than you were.

“You could make it better,” you said, smiling back. Hooking up with a stranger certainly wasn’t your plan for the night but fuck, another one of your friends was getting married and you were as hopeless as ever. Screwing blonde, tall and handsome over there would let you end the day on a good note at the very least.

“A woman who can drink and knows what she wants? Maybe tonight isn’t so bad after all,” he said, standing and walking down the bar, sliding onto the stool beside you. He licked his pink lips, wandering his eyes down to your own before finding your gaze. “Bet you taste delicious.”

“Go ahead,” you said, turning your body towards him and putting a hand on his chest. You sat up a little and leaned forward, your strange new friend moving the rest of the way, crashing his lips to yours. It was messy in those first few seconds as you learned how to fit his mouth against yours. He wanted to run things but you weren’t giving in so easy, your hand finding the back of his neck, dipping into his hair. His lips parted open in a smile, like you’d found some secret pleasure center he had, your tongue finding it’s way inside his warm and inviting mouth. 

He slowed down his invasion on your own and you matched suit, relaxing as you found a rhythm together. You were aware his hand was resting on your thigh, running up and down, slowly moving to the inside and sending a shiver up your spine.

“Take it outside,” said someone in the background faintly, probably the bar tender. He tasted like the bourbon you’d drank, smelled earthy and his scruff scratched at your cheeks in a way that made your nerves light up. “Hey. Outside now.”

“Come on sweetheart,” said your panting stranger, throwing you a wink before slapping down some money for both of your drinks. He grabbed hold of your hand and tugged you after him, leading you outside and to the mostly empty parking lot. You smiled when you saw he was taking you over to the beautiful black muscle car you saw when you entered the place not fifteen minutes ago.

“Nice car,” you said, watching him pull the back door open. He cocked his head like he got that a lot. He fell into the backseat, a sliver of doubt you barely caught in the those green eyes. You slid in beside him, putting his worries to rest and shut the door. The car was spotless and smelled like the leather had recently been cleaned. You bet this thing was fun to drive around on summer nights, windows rolled down, warm breezes filling the inside.

He didn’t say anything as his hand cupped your cheek, bringing your now plump lips to his swollen ones. It was softer this time, like he could let himself enjoy it now he knew he had time. You let your hands wander around his back, pushing his coat off his broad shoulders, feeling down the muscles that were hidden under a few more layers. He nipped at your lip, distracting you and making you melt back into the seat. He pulled you forward, trailing his thumb along your jaw, tickling the skin so your head tilted back. His lips left yours and started kissing their way down your neck, his hands unbuttoning your shirt. You tried to get him to go faster, your hand tugging at his belt but he tsked you.

“Uh uh,” he said, planting a harsh kiss to you again. You groaned, hands pushing his shirt off his shoulders. You ran your hands under his tee and moaned. He was smooth and firm and you needed that grinding against you more than you were willing to admit. Those beautiful lips pulled away and you found yourself hating when he did that more and more. But he ripped his shirt off and flashed you a devious smile, letting you have what you wanted finally.

“Fuck you’re gorgeous,” you said, reaching for him, crawling into his lap. He chuckled as he pushed against your chest.

“Boots,” he said, tracing patterns on your cheek as you felt your foot dig into his leg. You blushed when you realized how uncomfortable that was for him and quickly kicked them off, giving him enough time to compose himself. 

You looked at him as you took off your own shirt, leaving you in your bra and jeans. He reached for your waist, tucking your body against his, his free hand undoing the clasp with ease. You shifted so he could pluck the straps from your shoulders, the garment falling between the two of you for only a second before he picked it up and tossed it aside, landing somewhere on the dash from what it sounded like.

You didn’t have time to think about that before he was flipping you around, your bare back hitting the leather. He hovered over you, looking at you with a soft smile before continuing your make out session. He was so damn distracting you barely noticed those long fingers dancing down your chest, grazing the bottom of your breast. You inhaled sharply when he left the tiniest of touches on your nipple, giving the other the same treatment. Fuck this guy was serious about taking his time.

Your hips bucked up into his erection when he rolled the bud between his thumb and forefinger, twisting and pinching lightly until it was hard and sensitive, your body sweaty already. He broke the kiss to get his breath back, resting his forehead on yours as he gave the other bud some well deserved attention. He smiled to himself with closed eyes as you let out soft whimpers, your hand grabbing his wrist and sliding it down your body.

“Sweetheart,” he groaned, your hips grinding against his hard on, coaxing him into getting to the main act. You almost had him until his hand pressed against your hip, so much power in it you felt a rush of wetness between your legs. “Not yet.”

You bit your bottom lip when he sat up, keeping your hips still and undoing your jeans, yanking them down along with your black bikinis. He shuffled and his face appeared over your again. You leaned up to kiss him when you felt something rub along the inside of your thigh. You shuddered, his fingertips ghosting up your skin, setting your veins on fire. 

“Please,” you murmured, nipping at his bottom lip. He shushed you and you sank back into the seat, amazed to have met this stranger who knew how to wind you up better than even yourself. 

One long finger dipped through your folds, stopping at your clit and giving a slow circle around the bundle. You sucked in his exhale, the rush of pleasure in your fuzzy head making it feel a million times better. He rubbed slowly, listening to you pant and moan under his simple touch, kissing every inch of skin he could get to. You wished you could move your hips, get more pressure but this delicious torture was worth the wait. You already felt a burning simmer between your legs, heavy and ready to explode with what was surely going to be the best orgasm of your life.

“You’re so fucking beautiful,” he whispered, smashing his chest to yours. He was slick and his hair was sticking up, the windows fogged up with steam. You reached a hand between your bodies, undoing his belt slowly and pulling it from the loops. He groaned appreciatively and tilted his hips, giving you access to pull his zipper down. Your hands dug into the band of his pants and moved them, pushing them down over the curve of his ass and over his hard cock.

He was big and thick and swollen a perfect red, ready to pound into you until you were screaming you were sure. His head dropped to your shoulder as he brought both hands up, moving his weight off of you and looking down to line up with you. You wrapped your arms around his back, feeling his tip press ever so gently into you. You dug your fingers in and he slammed inside, your back arching and feet kicking against the door panel at the jolt of pleasure.

He pulled out nearly all the way before slamming back, eyes fluttering open to search for any sign of protest at the pace he was setting. 

“Come on baby,” you said, snapping your hips, a grunt falling from his lips. He winked and started to move, giving you a chance to settle in with him before you were bumping and hitting that sweet spot in you every single time. You let the moans and whines fall easily, clenching around him with each thrust, your blonde friend getting lost in you.

You were close but you planted your feet against the door, tilting your hips against him when he was buried to the hilt, a long groan tearing itself from him.

“Fuck sweetheart. You’re gonna make me come,” he said, his hand finding yours and intertwining your fingers.

“Come on,” you breathed out, the pressure in you almost unbearable, your mind focused only on holding off for him. “Wanna come with you.”

“Fuckin’ perfect,” he said, moving faster, throbbing and swelling inside you as your legs wrapped around him, heels digging into his ass to hold him deep. “Gonna…”

You squeezed around him one more time when he was buried as far as he could go, his mouth biting into your shoulder as he came hard. It was too much for you and you came too, shouting out and holding onto him so tight you knew you’d leave bruises. He pushed you both through until you were shivering from the high you’d just hit, panting the only sound to fill the car.

He pulled out and sat up against the door, chest heaving and smiling tiredly at you. You smiled and laughed, one finding it’s way out of him too as you both relished in the endorphins flooding your bodies. When you got some air back, you found your clothes, dressing yourselves quietly.

“Need a ride?” he asked. You cocked your head, knowing fully well he wanted you to say no.

“I’m good. Thanks for the…” you said with a laugh, waving your hand around.

“Fucking? Yeah, that was fun,” he said, helping you out of the backseat. You felt the rush of cool night air and saw a cab pull up, remembering you’d ordered one when you got to the bar. “That yours?” he asked. You nodded and he gave you a quick kiss on the forehead. “Night sweetheart.”

He walked around his car and climbed in, leaving without a second glance.

 

You regretted drinking that much that fast when you woke up in your hotel bed the next morning. Blondie though? You didn’t regret him. He was fun, even if you felt funny about the fact you’d never see that stranger again or know the name of the man that gave you the most satisfying sex of your life. 

You made a cup of black coffee in your room to wake you up and take the edge off. You were supposed to grab brunch with the bride and groom and after missing them both the day before, you were going to show up on time. You went through your routine fast, tossing your hair up in a messy bun, throwing on a pair of sneakers, jeans and your baseball tee, knowing you’d change again before the wedding party went out that night.

It was easy to spot your two tall friends in the lobby, sitting on the couch waiting for you. You hadn’t seen them in months and couldn’t resist sneaking up behind them. Jess let out a yelp and Sam jumped but rolled his eyes, already knowing it was you.

“Y/N! Don’t do that!” said Jess with a smile, throwing her arms open for a hug. You gave her a long one and then Sam as well. “What time you make it in last night?”

“Late,” you said, Sam looking around for someone it seemed like.

“Well at least we get to hang out with our maid of honor today,” said Sam, bumping into you. “Speaking of which, where the Hell is Dean? I told him ten.”

“The best man,” said Jess to you. You knew Sam had an older brother but that was about it. Jess had shared a few things about him with you that made you understand why it was a miracle he actually came. “It’s only a few minutes after, I’m sure he slept in. His car is here.”

“If he’s not down in five minutes, I’m-”

“Calm yourself, Sammy. Big brother Dean is here,” said a voice you recognized from somewhere. You spun around to watch Sam hug his brother, the brother giving Jess a hug as well before all three landed their gaze on you. Your eyes were wide and so were Dean’s when he saw you.

Hookup, backseat sex, blondie was staring right back.

“Y/N, this is my brother Dean. Dean this is Y/N,” said Sam. You took a step forward and Dean held out his hand to shake yours. You took his in yours, neither one of you saying a word as you tried to ignore the last time your hands were holding one another.

“Nice to meet you sweetheart,” said Dean, getting a neutral face on before the other two noticed. 

“You too Dean,” you said, looking up into those green eyes. Of course you had to go and screw the best man. Of course you had to screw Sam’s brother.

This was going to be the most awkward as three days of your life.


	2. Chapter 2

Catching up with Jess and Sam during your meal together was almost enough to make you forget about the other person at the table. Almost. Dean had made it very clear from your interaction that morning that you two weren’t supposed to know each other. You wouldn’t have minded getting it out in the open right then and there, laughing it off and putting it all to rest. But he just had to pretend he didn’t know you and you just had to do it right back. Now you were listening to Sam tell you about the time Dean put gum in his hair and all you could think about was how Dean liked little tugs in his.

You and Dean were acting like strangers which you weren’t sure how to feel about. He was a hookup. You’d never bothered to learn his name, he hadn’t asked for yours. Spending the next three days side by side wasn’t in the game plan when you got busy in his backseat. 

But fuck you might have actually  _liked_  him. You knew nothing about the man but you could have sworn that’s what the weird feeling you’d woken up with was. You wanted to know the stranger who could have kept his mouth shut last night but instead asked you how you were.

“Y/N? Hello, hungover girl,” said Jess, waving a hand in front of your face, snapping your attention to them.

“Sorry, what?” you asked, seeing the guys standing up, Jess slipping her purse over her shoulder.

“We’re heading back. You feeling alright?” asked Sam, putting a hand to your forehead. “You’re acting strange this morning.”

“I’m fine,” you said, moving Sam’s hand away. “Just tired is all.”

“Take a nap when we get back. Sam and I got some stuff we got to do. Maybe you and Dean can get to know each other later,” said Jess, waiting for you to stand up, probably thinking you were still drunk.

“Yeah, sounds good.”

 

As soon as the elevator doors shut at the hotel and you and Dean were alone, you groaned.

“Hey, I didn’t think I was screwing my future sister-in-law’s best friend last night. She’ll fucking murder me if she finds out. Or Sam will. Last night didn’t happen, got it?” he said.

“So much for last night being fun,” you said, leaning against the wall, Dean letting out a big scoff.

“ _It was fun_   _but_ …it was just some car sex. We’re both here for Sam and Jess. You and me, there’s nothing there,” said Dean, crossing his arms.

“Couldn’t agree more,” you said, feeling the elevator come to a stop.

“Then you got to not look like a deer in the headlights when you look at me,” said Dean. “You’ll tip them off.”

“Stop making a big deal out of it and it won’t be,” you said, stepping out into the hall, Dean following after. “Do you need me to pinky promise or what?”

“I’m just going back to my room. I’m tired too ya know,” he said. You walked in silence to the end of the hall, Dean going to the door directly across from yours. “We can be adults about this right? No hard feelings?”

“Dean, we’re good. Let’s both get some rest. We’ve got the party tonight after all,” you said, slipping inside your room and closing up before he could say anything more. He was right. It was just sex before. You were here for your friends and you were going to have a good time, no matter how awkwardly comfortable it felt to be around Dean.

 

“Can I get four beers?” you asked the bar tender, leaning up against the bar. “It’s on the Winchester tab.”

“Do me a favor, keep your boyfriend in line tonight, alright?” he said, pointing behind you to where Dean was all big smiles and lazy hugs.

“He’s not my boyfriend. Just in the wedding,” you said.

“Aren’t you supposed to hookup  _after_  the wedding, not before?” he asked.

“How much longer?” you asked, crossing your arms. He pulled out four beers and slid them over. You grabbed them and went back to the group, handing one off to Jess, one to one of her friends and reluctantly giving one to Dean.

“Thanks sweetheart,” he said, taking a long sip. You shook your head at him. No more sweetheart. Especially no more sweetheart when he was drunker than last night. “Wanna play some pool? I need a partner anyways.”

“Well with an offer like that,” you said, taking a cue from off the rack. You weren’t very good but Dean had barely been pointing the cue in the right direction. “I win, you don’t call me sweetheart anymore.”

“Alright, but if I win, you’re my sweetheart for the rest of eternity,” he said, holding out a hand. 

“You’re on Winchester,” you said, knowing you very likely wouldn’t see Dean after this weekend ever again. He let you break and after a few minutes, you’d sunk two balls. Dean took off his coat and grabbed his cue, a hard focus in his eyes, some of that drunkenness falling away. He sunk two balls on his first shot, another two on his second before throwing you a smirk. “You hustled me.”

“This was going to be friendly. You’re the one that made a bet out of it sweetheart,” said Dean, sinking another, walking around the table and pressing a fast kiss to your cheek before getting one more. He won in no time at all but managed to contain himself and not throw out a sweetheart at the end of every sentence.

“I got to use the bathroom,” you said, handing off the cue to one of the guys who wanted a turn. Jess and some of the other girls were in the bathroom, all three gushing over Sam. 

“Do you remember that time we almost set you up on a date with Dean?” asked Jess, laughing halfway through. 

“Well with everything you’d told me about him no wonder I said no,” you said, smiling even if you wished Jess would forget that ever happened. From the way you’d seen them interact with each other earlier in the day, it was obvious Jess and Dean loved each other. But you could very clearly remember how she said Sam’s big brother was a flirt, a one night stand type. Not the curl up with a blanket for date nights and introduce to your parents kind of guy.

“I’m glad you two are getting along. Dean’s always been a little bit of a loner when it comes to this kind of stuff,” said Jess. 

“This weekend is about you and Sam. If hanging out with blondie keeps you and Sam in a good mood, I got no problem with that,” you said.

“Blondie? I don’t think Y/N has  _any_  problem with hanging out with the other Winchester,” said one of the other girls with a giggle.

“Alright, I need another drink,” you said, popping out, the girls following after. You’d only been gone about five minutes but Dean looked actually drunk now and Sam was keeping a concerned eye on him. You bumped into him and Sam looked down for a moment before back at his brother. 

“He normally doesn’t drink like that unless he’s upset about something. You don’t think he’s got a problem with me getting married, right?” asked Sam. You scoffed and Sam eased.

“Dude, he loves you and Jess. He probably just wanted to cut loose,” you said, knowing Dean wasn’t in any position to drive. “I can take him back to the hotel, make sure he doesn’t do anything stupid.”

“You don’t have to babysit, Y/N,” said Sam. Part of him though very clearly wanted to take you up on that offer.

“Sammy…” you said, catching his eye roll. He smiled and gave you a hug. “I’ll take care of him.”

“You sure?” he asked.

“Yeah, I’m still pretty tired from last night anyways. Gotta catch up on some sleep for whatever this big fun game the future Mr. & Mrs. Winchester have planned for us,” you said. Sam chuckled and shook his head.

“Jess’ idea, not mine,” he said. “Give you guys something to do in the morning while we take care of last minute stuff.”

“Well I’m sure everyone will have a good time. Until then, I’m going to drive your brother back and make sure he gets in his bed safe and sound,” you said, heading over for Dean.

“His keys are in his front pocket,” said Sam. “I owe you one.”

“Night Sammy,” you said, giving him a hug. “Say bye to your super hot fiancé for me too.”

“Will do,” he said, leaving you to face Dean who was leaning up against a wall, not paying much attention to anyone in particular.

“Hey bud, want to head to bed?” you asked him. He hummed and nodded his head to your surprise.

“You drive,” he said, handing you his keys and throwing an arm over you shoulders. “You know what one it is.”

“Yes I do,” you mumbled, Dean keeping most of his weight off of you as you walked outside, the fresh air probably helping him sober up a little. You got him in the car without trouble and you wished you could have driven that car for more than the five minute drive back. 

You parked in the lot and stepped out, ready to help Dean up to his room when he sprang up and out of the car. You followed him as he walked inside and towards the elevators, a small wave of relief when you saw him headed for bed.

“I want to go swimming,” he said, looking back over his shoulder when he saw you by his side, taking off down the hall to where the indoor pool was.

“Dean,” you growled, trying to get him to come back as he already started taking his coat off. “Dean Winchester.”

“Oh, am I in trouble sweetheart?” he asked, definitely not as drunk as before now. You jogged to keep up and watched him open the door to go into the pool area.

“Dean-”

“I’m going swimming,” he said, taking off his clothes until he was down to his boxers, jumping in before you could stop him.

“Dean, get out of the pool,” you said. He shook his head and swam to the middle.

“Make me,” he said.

“You’re acting like child,” you said.

“No one said you have to stay,” he said, ducking his head under and doing a somersault in the water. “Unless you want to have a repeat of last night.”

“One of us has to watch your ass to make sure you don’t drown,” you said, ignoring his comment. You took off your socks and boots, rolling up your jeans so you could dangle your feet in the water. “You can play for fifteen minutes. Then I’m dragging you up to bed.”

“I’d rather play with you,” he said, splashing some water in your direction. You gave him a warning glance. “Take off your clothes and swim around with me. Not like I ain’t seen it before.”

“You ain’t seeing it ever again,” you said, watching him turn around. There were a few small bruises on his back from your fingers. You wandered your eyes down, taking in his back for the first time properly. 

“Aren’t we supposed to be getting along? Come on, fifteen minutes and then I’ll do whatever you want,” said Dean, twirling around in the water. You sighed and looked around. It was late and the odds of someone catching you both in there were slim. Dean started to smile as you undressed, slipping into the water as you were thankful you’d worn a black bra. 

“Fifteen minutes and then we go up,” you said, swimming over to him.

Fifteen minutes turned into two hours, hopping back and forth between the hot tub and cooler pool, splashing and floating, telling each other stories about Sam and Jess and how happy you both were for the two of them. 

“We should really get you to bed sweetheart,” said Dean when you yawned in the shallow end. 

“M’kay,” you said, another yawn escaping you. Dean laughed but stood up, taking you by the hand. “Dean…”

“Weren’t you supposed to be the one dragging me out little missy?” he said, helping you up the steps. You shivered, the air too cool for your taste. You headed back towards your clothes as you felt something warm be wrapped around you. “Come on, let’s sneak up before someone sees.”

“You’re fun,” you said with a soft smile, almost wishing you hadn’t said that. He returned it and you felt like inviting him back to your room. Someone walking by outside returned you to your senses though. “Thanks for the towel.”

“You look cold,” he said, grabbing his things and peeking his head out the door, waving for you to follow after as you ducked inside the elevator.

“I get cold easy. Chick thing I guess,” you said. Dean hummed and unwrapped his arms from around himself, giving you a hug from behind that certainly heated you up.

“Better?” he asked, resting his chin on your head. 

“Much,” you said. It didn’t feel awkward like it should have or like he was acting that way because of alcohol. If anything he was sobered up by now. But here you were, feeling as brave as the night before, both of you perfectly clear headed.

“That’s good,” he said, the doors opening. He kept close as you went to your rooms, lingering his hand a moment too long on your back to be just friendly. “Night Y/N.”

“Goodnight Dean.”


	3. Chapter 3

“Green team?” asked Dean, holding up a green bandana in the hotel lobby. You unfolded your wrapped up one, knowing the color the second Jess handed it to you. 

“Shocking,” you said, holding up a green one. Glancing around all of the couples had been paired off. It didn’t take a genius to see that you and Dean were a team.

“Okay, the scavenger hunt should take about four hours,” said Jess. “You can call the hotel if you get stuck and they’ll give you hints.”

“The winners get a free night here on us. Or if you’re Dean and Y/N, we’ll take you guys out to a nice dinner,” said Sam. 

“Trust me, we aren’t gonna win,” said Dean. You were surprised with how confidently he said that. Dean seemed like a smart guy after all.

“Alright, we’ll see you guys later,” said Sam, ushering everyone out of the building. You and Dean walked over to his car, sliding inside and reading your first clue.

“Bar,” you said in unison, Dean heading down the road, watching the other cars take off in different directions.

“So, you uh, nervous about giving a speech tomorrow?” he asked. You shook your head. “That makes one of us.”

“It’s your family Dean, you’ll do fine,” you said, patting him on the leg. “If you turn to a pile of mush, which you won’t, just wink at me or something and I’ll help.”

“Really?” he asked. “You’re awesome.”

“Just tell an embarrassing story and then say how much you love him. That’s all there is to it,” you said. “It won’t be hard.”

“I know. I psych myself out of stuff like that sometimes, ya know?” he asked.

“I got your back. It’s kind of our jobs to look out for each other during this whole thing isn’t it?” you asked. He nodded once but was quiet as you drove. The two of you spotted the little white and gold balloons near the bar entrance as you ran out to grab one of the cards with the next clue. You tore it open when you were back in the car and started reading it when you saw Dean’s fingers wrap around your wrist.

“Sorry for being a dick last night,” said Dean, your head popping up. “I made you miss being with your friends.”

“It’s fine. I got to hang out with my new one,” you said, smiling at him. You handed over the card. “What do you think? This one’s got me stumped.”

It wasn’t that hard to figure out it was the local park you were off to next but Dean seemed sullen that morning. Maybe letting him win this silly game would make him feel better. He read it over for a minute as you realized he was still resting his hand on your arm. You moved yours away, pretending like you had an itch on your other one.

“I say we check out the park,” said Dean, pulling his hand back and heading out again. The park was a little longer of a drive so Dean turned on the radio. You rolled down your window and stuck your hand out, making waves in the air, hearing a tiny chuckle from Dean when he thought you were lost in your own head.

“Looks like the place,” you said, spotting another set of balloons. Both of you got out that time, stretching out as the warm sun tickled your skin. 

“Um, I ain’t got a clue on this one sweetheart,” said Dean, holding up the card and handing it over. You thought he was doing the same thing you’d done for him but you quickly scowled. “…and you don’t know either. So now what?”

“We could get a hint,” you said, looking around the nice looking park.

“Or we could ditch,” said Dean. “Unless you’re really into this.”

“There’s ice cream over there,” you said, nodding to the little stand not too far off. Dean smiled and shoved the card in his pocket. You walked over together, enjoying a light breeze, ignoring how Dean’s hand kept brushing up against yours as you walked.

“Two chocolates,” said the man, handing over the cones. You glanced down at your simple sundress, patting the pocket and finding your room key and phone but nothing more. 

“I got it,” said Dean, paying for you both. You sighed and walked away, leaning against the railing over the small bridge down the path, trying to keep your ice cream from melting all over your hand. “Hey,” he said, ruffling your head with his free hand when he joined you. “What’s wrong? It’s only a dollar.”

“Yeah but you paid for drinks the other night too,” you said. Dean stopped moving his hand for second before sliding it down and around your shoulders.

“You worry too much. I wanted to do that too,” said Dean. You relaxed and ate your ice cream, watching a few ducks swim around in the water, two in particular looking like they were playing with each other.

You’d like to play with Dean in a pool again someday.

“You’re living in Texas?” asked Dean, leaning over the railing with you. You hummed. 

“It’s different than the east coast but I like it. Simpler and all that,” you said.

“I’m in Kansas. We could hang out sometime ya know. Give you a call when Sam and Jess come to visit so we can get together,” he said. Sam and Jess. You two were only ever going to be friends in his eyes. Which was exactly the logical thing to do, to keep it simple and nice and not awkward.

But the awkward thing was being around him didn’t feel awkward. It was like talking with Jess, with your best friend, but better. It was like being around someone that made you smile for no reason at all. Dean kept doing things that were definitely skirting the friendship line and neither one of you seemed to bring it up.

“When was the last time you were on a swing?” he asked, pulling you from your thoughts. You glanced over to a pair of them, Dean already taking hold of your hand and pulling you with him.

“Dean, I’m an adult,” you said, tossing your cone in the trash along the way. Dean chuckled but you let him guide you over and sit you down on the hot seat. He moved behind you and pulled you back, giving you a push, your feet kicking out like second nature. “Alright, maybe this isn’t such a bad idea.”

“Told you so,” said Dean, taking a seat next to you, kicking himself off. You must have sat on those swings and talked for hours, laughing and making inside jokes. Only this time you weren’t talking about Sam and Jess. It was the two of you, sharing stories, going off on tangents about favorite movies and winding up at Dean’s love for pie. You would have stayed on those swings forever if Dean’s phone hadn’t rung. “You’re on speaker Sammy.”

“I’m impressed with your guys’ commitment to the hunt and everything but it’s after four. Rehearsal starts at six,” said Sam. You and Dean panicked as you realized you’d spent the whole day there, quickly hopping off and rushing over to the car. “You two totally forgot, didn’t you.”

“We’re on our way back now. We’ll be there Sammy,” said Dean. He was taking off in a flash and getting you back fast, the both of you practically sprinting through the hotel lobby. 

“Dean, you going to drive yourself?” asked a man’s voice as you ran through. “We’re taking off in ten minutes.”

“Dad I’ll be there on time, relax,” said Dean, waving you forward as you held the elevator for him. You got your breath back as you went up, Dean cursing under his breath. “I’ll drive you.”

“Thanks,” you said. “I’ll be about thirty minutes. If it’s too long just go without me. I’ll get a cab.”

“I’ll wait. Green team sticks together,” said Dean, untying the bandana from his wrist as you recalled you were still wearing yours. You untied it and frowned when you saw the strange tan line. “No one will notice.”

“You did,” you said, rushing down toward your room with Dean in tow.

“Trust me, no one looks at you the way I do. You’re fine,” he said, opening the door to his room. “I’ll be down in the lobby.”

Thirty five minutes later you were rushing out of the elevator, still ignoring the comment he made, your heels in hand as you spotted the back of Dean’s head.

“Sorry, I know I’m late,” you said, walking past, spinning around when you didn’t hear him follow. “Come on De-”

He was wearing a suit. Tie loose, nice and relaxed, but still he looked good. You would have blushed at the way you stopped mid sentence if Dean wasn’t devouring you with his eyes. It wasn’t even a new dress but it was simple and black and apparently enough to make Dean’s eyes turn that same shade of green as at the bar.

“We should get going,” you said, breaking the two of you out of your haze, your feet burning a little on the hot blacktop. You wiped off your feet and slipped on your heels in the car, Dean staying quiet as he got you both there with two minutes to spare.

“Not late,” said Dean to Sam who was waiting outside. Dean put a hand on the small of your back as you tried to rush, nearly tripping up the steps if he hadn’t caught you. “Don’t break an ankle sweetheart.”

“Alright, let’s do this.”

 

The rehearsal went well, not much to it on your part. Dean would walk you down the aisle last before Jess made her way down. She hadn’t bothered with a train so you wouldn’t have to deal with making sure if looked nice in the back. It would be simple really. 

A little after seven you, along with most of the guests, were at the hotel restaurant meant for a simple dinner. After the food was done though it quickly turned into a party, people dancing and having fun like the reception was happening tonight.

“Bourbon?” asked Dean, handing you a drink. You laughed as you took it, the two of you leaning up against the wall. He grumbled when an older couple walked over with smirks on their faces.

“Dean, aren’t you going to introduce us to your friend? We haven’t seen you all weekend,” said the man, with a teasing smile. 

“Y/N these are-”

“Your parents? We’ve met. I think your dad is just fucking with you,” you said, giving Mary a hug. “Long time no see.”

“Not since New Years. I didn’t realize you and Dean knew each other,” said Mary. Dean opened his mouth but nothing came out. Was he…embarrassed? 

“Yeah, we met a few days ago. Yesterday,” you said quickly. You could imagine why Dean had that reaction though. You knew all the Winchesters, had spent time with all of them too, except for Dean that was, the one who never wanted to come to anything. The loner all because of what? Having a reputation for not settling down? “Hey, let’s go dance,” you said, bumping Dean with your elbow, putting your drink down and pulling him after.

You threw your arms around his neck as his fell over your hips, swaying lightly.

“Thanks. I don’t know what that was,” he said, looking away. 

“Parents mean well but…I got your back,” you said, taking a step closer. Dean hummed and rested his head on your shoulder, the two of you moving together for one song and then two and then three, never breaking apart.

You took a break and had some more drinks, back and forth between that and dancing, having a good time as that feeling of bravery rushed over you again. You were mid laugh from something he’d just said when you caught his face. He was cupping your cheek and pulling you into a kiss in no time, moving his lips the way you liked.

“Dean, no,” you said, pushing him away, looking up. He was confused in one second and disappointed the next. “I’m going up. I’m not making the same mistake twice.”

You brushed past him and out through the lobby, headed for the elevators. You had just spun around inside when Dean was there, ducking in after. You looked away and back at him, no disappointment in those green eyes now.

“Why exactly am I fucking mistake?” he asked, towering over you. You rolled your eyes and waited for the door to open, glad to get away. “Hey!”

“Drop it Dean,” you said, knowing he was right on your heels. You got your door open and were ready to slam it but he was there, stepping into your room. “Get out.”

“I asked you why I was a mistake,” he said, backing you up against a wall. You looked to the door but he wasn’t budging. “I want to know.”

“Fuck Dean, because Sam and Jess’ wedding is tomorrow. Your brother’s wedding. My best friend’s wedding. This is their day. This is about them. You were just car sex. The rest of it was the universe flipping us off. You didn’t want more. We aren’t anything,” you said. Your stomach dropped at saying that. You were lying if you said you didn’t like him, that he didn’t make you feel certain things that scared you in a good way. Dean was the one that made it clear you weren’t more. He didn’t get to say he changed his mind because he was drunk and horny again.

“Y/N,” said Dean, holding your face in his hands, kissing you long and slow. Maybe you were wrong, maybe he wasn’t doing this because he wanted another hookup. “You…”

“Dean?” you asked, his forehead resting against yours, warm breath spilling over your face. He pulled back and made his eyes hard, moving his hands away.

“You…you were the worst decision of my life. All because my drunk ass felt sorry for that sad, pathetic face. God knows why,” said Dean, clenching his jaw, not caring at all how you couldn’t look him in the eye. “Tomorrow we can be civil and then go our separate ways.”

You couldn’t find any words so you simply nodded, jumping as he slammed your door shut. You got out of your dress and in the shower on autopilot, hoping a cold shower would bring you back to yourself. If you’d learned anything about Dean over the past few days, it was how poorly he felt about himself. You had to call him a mistake when you thought anything but, when under any other circumstances you’d be walking over to apologize and trying to fix whatever new emotional scar he was surely going to carry with him.

You would have gone over.  _You wanted to_. But Jess warned you years ago about Dean. He had said it himself not five minutes ago. He was drunk that first night. He was drunk tonight. He didn’t  _actually_  want you, only a warm body to spend the night with.

So why did it hurt so much?


	4. Chapter 4

Being civil was a lot easier than you thought it would be. You and Dean pretended like nothing happened during the wedding, focusing on Sam and Jess instead. It was going really well in fact. Until you had to take stupid pictures.

You pretended like Dean was someone else when you had to take some together, like you were some happy person. No one made any comments that you looked grumpy though so at least that was a good sign. Eventually that slow torture ended and you gave your toast, Dean giving his, the dancing starting again.

“Hey Y/N? Can you do me a favor?” asked Sam, looking happier than you’d ever seen him in his life. 

“Anything for the groom, what’s up?” you asked, Sam pulling you away from the reception and out through one of the hotel halls.

“I can’t find Dean. They were looking for a family photo,” said Sam. “Can you help me find him?” 

“Put those puppy dog eyes away, of course I’ll help Sammy,” you said, seeing the relief wash over his face. You followed him down the hall, Sam checking on one side, you the other until you came to the back balcony deck. “Found him.”

Dean was holding a drink, leaning over the railing, staring out at nothing in particular. Sam opened up the back door, bringing you with him.

“Hey Dean,” said Sam. You felt a light shove on your back that made you stumble into Dean. By the time you were spun around, Sam was closing the door back up.

“Sammy what are you-”

“You two are allowed to come back to the wedding when you talk this out,” he said through the door. You saw Jess come down the hall, waving for Sam.

“Jess unlock-”

“Talk you two!” she said, smiling as she and Sam left you there with Dean. You looked around. There was no other way off the balcony. You grumbled and moved to the railing, looking over and knowing it was too far of a drop.

“Here,” said Dean, offering you his glass. “You look like you could use one.”

You stepped to the side, putting some space between you. Dean took one to match and held out his drink again. 

“It’s your favorite,” he said. You shook your head but took a small sip anyways. “Yeah, I fucked up big time.”

“Was I just sex to you?” you asked, doing your best to keep your voice light. It really was an honest question. You wanted it out in the open for good though.

“I told you the truth last night. You were the worst decision of my life,” said Dean. 

“Oh,” you said, feeling small and throwing away that ‘you liked him’ speech you had in the back of your head. You looked down, pretending to be distracted by the lawn below, something to make the awkward tension pass.

“That probably came out a lot worse than I meant it to,” he said, pushing his glass to the side. 

“How’d you mean it to come out,” you said, picking at a petal on your corsage.

“It’s pretty. You shouldn’t break it,” said Dean, gently pushing your hand to the side. “Jess and Sam cornered me a little while ago, told me to stop breaking pretty things myself.”

“What-”

“She’s your best friend. He’s mine. We weren’t fooling them,” said Dean. You turned your body away, long fingers interlacing themselves with yours. “Ever act a certain way because you’re scared? Do some really stupid shit because you don’t know how to grow up?”

“Yeah, I do,” you said, twisting your body back, looking down at his hand in yours.

“Ever have sex in the back of ‘67 Chevy and regret it?” he asked. “Wish you could go back and talk instead? Do things the right way?”

“I was the one that flirted first,” you said, risking a glance in those green eyes. None of the hard anger from the night before was there. Just…a sad calmness that made you tilt your head.

“I saw you first,” he said. “I could have said we’ll do this another time. I can take you to lunch. I could have done a million things different instead of kissing you but damn I wanted to. I still do.”

“I’m the worst decision of your life,” you said, a pang of hurt crossing his face.

“Worst, best, one in the same. That mean stuff, yeah, that was a lie to try and make you feel as bad as I did. I’m sorry about that,” he said, bumping into your arm. “I liked you. I don’t like women. I have sex with them and then go off and brood. You though…I don’t know what the Hell it is but you just…God I wanted to know your name so badly, try and find you again, just to say hi or  _something_. I wasn’t expecting to find out you were sleeping across the hall.”

“We’re kind of dumb. Worrying about Sam and Jess, taking away from their day when Butch & Cassidy in there are trying to get us together,” you said. He hummed, softly, and you knew he was hurting from your words last night. “You were a mistake.”

“Yeah, I got that,” he said, trying to let go of your hand, snapping his head down when you held on tight. “Um you got to-”

“It’s like…you were…like water in the desert if you want to go with crappy analogies. I don’t know. But it was just…everyone after you…I was going to compare them to you, to how easy it was, how good it felt. Nothing’s going to be as good,” you said, the resistance in his hand falling away.

“Can I keep you?” he asked, smiling. You couldn’t keep down a laugh and he took a step closer, turning his body so you were facing one another. “I’m serious. I always blow off that feel good stuff when someone says it but I actually believe you which is kind of amazing for me.”

“I like you,” you said, lighter and happier than you’d been all day.

“I like you too sweetheart,” said Dean. “Look at that, not so hard after all.”

“Nope,” you said, taking a small step forward. “Are you really going to call me sweetheart?”

“I recall someone losing a bet and getting to be my sweetheart for all eternity,” said Dean, moving your hands up to wrap around the back of his neck, his coming down to rest on your hips.

“Eh, whatever you say baby,” you said, feeling Dean burst out laughing. “What! You liked it in the car!”

“It was also hot as Hell in that backseat. You’re kind of rocking sweet girl next door right now in that dress,” he said. “I was expecting a ‘honey’ or something-”

“Girl next door? Remind me of that the next time you’re naked and under me,” you said, Dean moving to the faint music coming through an open window somewhere. “You look good in a tux by the way.”

“Isn’t sex what got us into trouble in the first place?” he asked, spinning you around, pulling you back into his body.

“I think the us being stupid got us in trouble. The sex was the easy part,” you said. “We should try to behave. This is a wedding after all.”

“Wouldn’t be a wedding if the man of honor didn’t get together with the maid of honor,” said Dean. You laughed and he cocked his head.

“Alright,  _man of honor_ ,” you said, feeling his groan vibrate through his chest. 

“Shut up. You make me nervous,” he said. You raised an eyebrow and he gave you a smirk in return. “In a good way.”

“I understand completely,” you said, moving your hips slower, letting yourselves enjoy it like you’d wanted to the night before.

“You don’t think they’ll forget we’re out here, right?” asked Dean. 

“Knowing Sam and Jess and how busy they are, I’d say we’ve got a fifty percent chance they completely forget,” you said.

“I hope not. Our time out can’t last forever,” said Dean. “Not that I mind the company I’m with.”

“We got a glass of bourbon and some music on a nice summer night,” you said, Dean getting riskier and moving the two of you around more.

“You’re right. This is better,” he said, pressing a sweet kiss to your lips. You would have loved to make it longer but the sound of a creaky door and two grunts from the door caught your attention.

“I think they worked it out,” said Jess, holding up her hand and getting a fist bump from Sam.

“Got their heads out of their asses you mean?” said Sam. “You’d think they’d remember how we couldn’t stand each other when we met.”

“You two were gah gah for each other the second you met. Everyone knew it,” said Dean shaking his head at them.

“Wow. Huh, you guys wouldn’t know  _anything_  about it seeming different on the other side now, would you?” asked Sam with a smirk. “Did you not think we’d approve?”

“We tried to get you two together years ago! We were  _kind of obvious_  we thought,” said Jess, your face flush but you didn’t mind.

“You’re cute when you blush,” said Dean, eyes scanning over your cheeks. 

“Shut up baby,” you said, a snort bursting out of him that made you smile. “Are we allowed to come back? We won’t be grumpy anymore, promise.”

“Sure but first we want one more thing,” said Sam, taking off down the hall. He was back a minute later with the photographer. 

“Of course,” you said, waddling back with Dean’s arms around your waist. You smiled, a genuine one. You didn’t hear the camera go off and looked up at Dean, seeing him look down at you. You heard a shudder snap and laughed.

“Oh you fucking assholes doing that cutesy shit on purpose,” said Dean, his cheeks turning a light shade of pink. You heard a few more photos go off as you settled down and took a few more of the two of you and then with Sam and Jess. “Can you get just one of her?”

“ _I think someone likes you_ ,” said Jess in your ear. You pursed your lips together but Dean shook his head as they stepped away.

“Relax, like the camera isn’t there,” said Dean. You cocked your head, like how was that possible. He went over to the camera guy and he left. “He’ll do it later.”

“Alright, let’s get back to this wedding.”

 

“Where’s your shoe?” you asked when you got up the next morning, giggling as you leaned over the bed, trying to wrap your sheets around yourself from the chill in the room.

“Where’s your bra? I  _distinctly_  remember enjoying removing that from your body,” said Dean, laying lazily on his stomach, a tiny sliver of sheet covering his bare ass.

“I enjoyed that too,” you said, plopping down next to him, touching your side against his, tugging his sheet away and stealing it for yourself. 

“You just like me naked,” he said, throwing an arm over you. You hummed.

“Yes I do. I like you too,” you said, resting your head in your arms as you turned to face him. “Such a cute butt and freckles. I couldn’t see those freckles in the dark.”

“If you want to talk about cute butts…” said Dean, pinching your sheet between his fingers and pulling it away. “I know a gal with a cute little one,” he said, trailing his finger over one of the cheeks.

“Ugh, I want to stay in this bed with you,” you said, whining when he nodded and sighed.

“You’ve got your flight soon. Not to mention pack and everything before I drop you off,” he said, moving his hand up your back and giving you a quick kiss. 

“You don’t have to do that,” you said, catching his eyebrow raise. “Sorry, not used to having a boyfriend.”

“The few times I was one, I was shitty at it,” he said, rolling out of bed with a groan. “Shit, I thought you were gonna be the one that couldn’t walk straight. You know how to treat a man good.”

“Just a little tease for you to bide you over,” you said. You watched him gather up the articles of clothing he could see. “We’ll be okay Dean. Long distance is going to take some getting used to though.”

“We’ll make it work. Call everyday, get our Netflix on at night, visit when we can,” said Dean.

“I found your shoe,” you said with a grin, staring up at the top of the dresser when it sat with your bra nearby.

“Visit  _very_  often,” said Dean with a grin, handing it over to you. “It’s only a seven hour drive.”

“We can work with it.”

 

It’d been a week since Dean dropped you off at the airport and you already knew you couldn’t live with it. You wanted him there. Especially when there was a bug on the wall that one night and you really didn’t want to have to deal with it yourself.

You were sitting on your couch with your laptop up, looking for jobs in Kansas, thinking how ridiculous you were being at thinking about moving after only a week of dating. Dean would tell you that you were rushing too fast, probably say something like you were being clingy. Well, he wouldn’t say that, he was too nice to say that. You didn’t want to be clingy though, you just wanted to be near him. 

“I need takeout,” you said, pulling out a menu from your everything drawer and ordering way too much. You were stuffed and thought you’d found a few good options when Dean’s face lit up on your phone for your nightly call. “Hey.”

“Hey, sweetheart,” he said. “How you doing?”

“Okay. Eating some Chinese food,” you said.

“Order enough for two?” he asked. You spun around in your seat just in time to hear your doorbell ring.

“You drove all the way down here on a Tuesday?” you asked, running over to the door.

“Sure did. I had a job interview,” he said when you opened the door. You looked him over, wearing his normals jeans and plaid you’d seen him in during the wedding only slightly dirtier. “My buddy Benny opened up a new garage in town a few months ago. He could use an extra set of hands around there.”

“Wait, so you’re-”

“Yup. I’m staying with him for a while. He’s only a ten minute drive. A lot better than seven hours,” he said, smiling wide. “Sorry but that smells amazing and I’m starving,” he said, walking inside, kicking off his boots.

“There’s plenty,” you said, waving him over to your table as he looked around. “What?”

“Are you…are you listening to Zeppelin?” he asked, hearing the low music playing from your computer.

“Uh, yes? You don’t like rock?” you asked, positive you must have talked about music at some point during your short relationship.

“I think I’m in love with you,” he said, scooping you up in his arms.

“I think I just might be too,” you said, laughing as he sat you down. You grabbed a plate for him and handed it over, spotting him hang up his phone and set it down but not without catching the picture in the background. “Is that me?”

“Mhm,” said Dean, sliding his phone over. It was from the wedding, one of you alone, definitely candid as you gave someone a soft smile. 

“It’s pretty,” you said, normally not one for liking pictures of yourself. 

“I thought so,” he said, munching down on his dinner. “Sam texted me a few more.”

“I like this one,” you said, flipping it around, one of you and Dean hanging out on the back deck again, the string lights on, sitting on top of the railing talking. The way he was looking at you and you were giving it right back…

“Apparently we’re very deeply in love. Why are we so stupid again?” asked Dean, laughing to himself as you picked up your computer and put it on the table. “What’s that?”

“I was job hunting but you beat me to it,” you said. “Apparently we’re very deeply in love.”

“Zeppelin, take out for dinner, makes me feel good, down for car sex…yeah I’m about you in one of my band tees away from being in love with you,” he said, catching your smile.

“What was that sweet thing in there? The feeling good?” you teased, running a hand through his hair.

“You’re gonna feel  _amazing_  in about an hour after I eat and this food settles,” said Dean.

“Oh you better,” you said. “And uh baby?”

“Yes?” he asked, no laugh this time.

“Where can we find one of those band tees you were talking about?” you asked, whispering in his ear.

“I’ve got one in my duffle in the back of Baby,” he said. 

“Did you have plans with Benny?” you asked, watching his head nod. “After dinner then, why don’t you go grab your bag and you can spend the night, see if you can get me in one of those shirts.”

“Anything for you sweetheart.”


End file.
